16 Anecdotes From The Worst Sexual Encounters Of The Last 50 Years

Ah, sex. The good stuff. The Granddaddy of them all. Even when it’s bad, it’s still good. Just ask the dozens of fine ladies (and some gentlemen, perhaps? When the lights are off, who can tell really? It’s 2016, people.) who have had a go-around with ol’ Holt.

Some folks have had a less pleasurable experience than others — and you need not to search further than the content barracks in the dark corners of Reddit to find the legitimately cringeworthy goods. I’ve read some disturbing shit in my life, but nothing will ever come close to what these random internet strangers have done during sexy time.

He came instantly, left the room and didn’t talk to me (out of embarrassment) for two weeks after.

Nothing to be ashamed about, my man. If you’re not a two-pump chump, you’re not trying hard enough.

I’d dated this guy for a few weeks. Then came sex time. We were naked and making out, then I moved to go down on him. His crotch smelled very strong of cologne, and never dealing with it before, I started sucking him. It was cologne, and a lot of it. My mouth was full of it, my eyes & nose started to burn, and I started throwing up. I couldn’t get that taste out of my mouth and off my face for days. It was Drakkar Noir.

Guys, don’t ever fucking do that.

And they say chivalry is dead.

I met a guy on eHarmony. After our second date, we went to his apartment to, basically, get drunk and have sex. He goes down on me and after a few minutes, I end up in excruciating pain. I look down and see blood everywhere. He bit off a piece of my fucking vagina.

Don’t ask me to eat you out if you don’t actually mean it.

Was having sex, she was riding cowgirl with lots of bouncing. Perhaps I zigged when I should have zagged. Long story short my boner got right angled. I had a n ugly purple-ish golf ball sized knot off the side of my dick for about 3 days. Then when the swelling went down, the bruising started to spread out…right down too my balls. My balls didnt hurt, but they were an ugly color. Only time in my life I googled “broken penis”.

TL;DR : Dont get your dick bent.

Never zig when you should zag.

My girlfriend was going down on me after drinking orange juice. She took it a little too deep and puked, forcing a unique bile/OJ mixture into my urethra. 0/10, would not recommend.

Taking the term “oil change” to a whole new meaning.

She asked if I wanted a blow job. It immediately began with this weird sensation so I looked down and realized that a.) she had never done anything like this before in her life, and b.) she took the term ‘blow job’ as literal and was trying to inflate my dick like it was a balloon.

I bet she makes some killer balloon animals, though.

I was enjoying myself and said “oh shit yes!” and she stopped the sex to tell me not to swear. She was a bit of a prude. 5 minutes back into the sex she says “talk dirty to me!”

I didn’t really say anything. I didn’t know how to talk dirty without swearing. “good to be here”?

“Good to be here” is quality dirty talk.

Farted in a 69 with an obese girl, left and fell down the stairs and ended up in hospital

Just your run-of-the-mill 69 experience.

he rubbed his dick between my butt cheeks until he came, not realizing he wasn’t actually in me.

Close enough.

With my ex bf. I’m a pretty small person (5’0 and 95lbs) and he is big, plus had gained weight (6’3 and 250lbs). He was on top of me and refusing to use his arms to support his upper body, causing him to rest his entire chest weight on me. I kept telling him to prop himself up, but he kept saying his arms were tired. I was basically suffocating. I started wheezing very loudly and needed my emergency inhaler. To make things worse, he got mad at me for “ruining the moment”
TLDR: Fat bf gives me asthma attack

At least let him finish.

Her blowjob technique involved a lot of teeth. She also tried to ‘deepthroat’ me, which just ended up painfully bending my dick, since she didn’t quite understand the ‘throat’ part.

She complained about being too wet, she complained about having orgasms too soon, complained about liking me too much, complained about being in too many positions, complained about going to work in the morning, etc etc.
It went from seeming funny to just being annoying.

Kick her to the curb.

I had a girl start giving me a blowjob and we were both pretty messed up. She gagged and threw up a little on my cock and I closed my eyes pretending not to notice while she slurped it all back into her mouth and swallowed it.

Was not the best experience, 8/10 would recommend for the story

What a Goddamn trooper.

Girlfriend was cold during sex. She decided to pull the quilt tighter which ended up with me head butting her in the nose.

Sounds tame. Unless there was blood, 0 stars.

He was humping my leg like a chihuahua and made out like a Lickitung had no control of half of its tongue. Yeah.

Did he bark?

Oral on a woman, unexpected diarrhea, explosive orgasm, you do the math. (Please, for the love of all that’s holy, don’t show your work.)

I was 15, and snuck away from a end of the year house party with a well known village bicycle type girl. Drunk, and excited to lose my virginity we ended up having sex at a nearby elementary school playground (TDornM).

As I got close to finishing, she goes “Lou, I want you to cum on my tits” then wrapped herself around my legs like a pretzel, tits in the air ready for my blessing. I blow my load and suddenly hear, “YOU MOTHERFUCKER ITS IN MY EYE!!” I look down and sure enough she was wearing a brand new pair of bukkake sunglasses.

I was doing #buttstuff with a chick and she kept saying “hurry baby” and I’d never been told that so I was pretty pumped. Well when I finally came and pulled out my dick was covered in shit and cum. Almost ruined me on #buttstuff. Almost.

The guy that farted while 69’ing a fat chick fucking deserved what he got. It’s one thing to get drunk and have an accidental quickie and then bounce. Whole different ballgame when you actually put that much effort into sex with a whale.

Went home with a girl when I was borderline blacked out, after about a half hour of trying to finish the evening as one would expect such an encounter to end, I just gave up, resigned to the fact that the ole’ whiskey dick had gotten the better of me. She started sobbing, thinking it was because I wasn’t attracted to her. I felt like such a scum bag, trying to explain to her the effects of copious amounts of alcohol on the male reproductive system. Also, though, she was half right.